Bad sort order in file picker, correct in Finder

Question

Say I download a bunch of random files in Safari for upload to some other website. The files automatically end up in my Downloads folder, so it would make sense to sort the files by Date Added so the stuff I just got will be at the top of the list for easy selection.

Problem is, this doesn't happen. In fact, I don't see any rhyme or reason to what I'm getting here:

Note that I'm sorting by Date Added, descending, so the items from today should be at the top of the list. Instead they're halfway down the bottom and jumbled in with a bunch of other items. Under a "2012" heading. For a file that was downloaded today.

If I open the Downloads folder up in Finder and apply the same sort, the files appear correctly:

This strange behavior happens in every application that uses the system file picker.

Any idea what's causing this and how to fix it?

Answer 1

Finder and the file dialogs have had two different sorting modes (sort by and arrange by) since 10.7. In the first screenshot, the arrange by mode is probably set to date created or date last opened. Try changing it to none instead:

The menu shown above changes the arrange by mode and clicking one of the header columns changes the sort by mode.

Answer 2

For macOS Monterey

The default order for sort and the default selection for arrange are not shared between Finder and Open/Save file dialogs. The settings must be specified in each case separately.

However, the button in the Open/Save file dialog does double-duty for Arrange and Sort, depending on whether you hold down the ⌥ key or not, as described by the hover tooltip. Hold down the ⌥ and click the button to set the sort order for the Open/Save file dialog.

Here is the button's default function. The heading is "Group items by:".

Here is the button's function while holding down ⌥. The heading is "Sort items by:".